On arrival in the city you will be met and transferred to your hotel once you get to the city, look up and there it is: the famous Chicago skyline set against the sweeping shore of Lake Michigan. You’ll quickly appreciate this urban-meets-natural beauty when your feet hit the ground in the nation’s third-largest city. In the heart of the Midwest, Chicago boasts soaring skyscrapers, 77 colourful neighbourhoods, 42 kilometers of lakefront with 26 beaches and 580 parks and green spaces. Equally impressive are the dining options – 7,300 restaurants and more than 65 craft breweries – outstanding arts and culture, urban recreation along the waterfront, world-famous events and a vibrant, inclusive spirit.

This cosmopolitan playground is bursting with things to do. Sightseeing options range from Chicago icons like Millennium Park’s sculptures, fountains, gardens and event spaces to awe-inspiring architecture by Frank Lloyd Wright, Frank Gehry, Daniel Burnham and Louis Sullivan. Get above it all on The Ledge, a glass platform on the Skydeck at Willis Tower, or the 360 Chicago Observation Deck on North Michigan Avenue, where the TILT experience leans you out 300 meters above Michigan Avenue.

Take in the beautiful cityscape with a stroll along the Chicago Riverwalk, where you can enjoy a waterside meal, sip a drink or set out on an architecture cruise on the Chicago River. Take the children to Lincoln Park Zoo, Navy Pier and Wrigley Field, three iconic and family-friendly attractions, or rent bikes and pedal along the 29-kilometer Lakefront Trail.

Today its time to collect your car and embark on the journey of your lifetime along Route 66.

As you journey toward Springfield along the Illinois Route 66 National Scenic Byway, the capital of Illinois, you will go through some wonderful towns, each with its own unique attractions, historical icons and Route 66 nostalgia!

The capital of Illinois, it’s best known for being Abraham Lincoln’s home for the 17 years leading up to his election as the 16th president of the United States and for its strong connection to historic Route 66, which runs right through town. It's the perfect stop for history buffs and families.

The two most famous places to eat on Route 66 in Springfield are the Cozy Dog Drive-In and The Chili Parlour. You can’t miss the iconic “FOOD” sign outside the Cozy Dog Drive-In, which claims to be the first place to have served corn dogs. Open since the 1940s, this is a traditional Route 66 diner, souvenir shop and mini-museum. Enjoy a classic “hot dog on a stick” while browsing through the great collection of Route 66 souvenirs and posing next to the old gas pump. Next, be sure to visit The Chili Parlour. The owner, Rose, is delightful, and you can get their famous chili just the way you like it: mild, medium or super-hot, and with or without meat.

In Springfield you’ll also find the Route 66 Drive-In. Open from the end of May until the beginning of September as well as weekends in October, this twin drive-in plays two movies every night. This is the old style of watching a movie – pull your car in, park, fill up on snacks from the concession stand and watch a movie on a large screen while sitting in your car. Nothing is more classically American than this.

Fans of antique cars, cool custom cars and other show vehicles should attend the International Route 66 Mother Road Festival in Springfield. Every September, the state capital cranks up its engines and attracts fans from every corner of the globe. This car festival and show pays homage to the cars that drive (or once drove) the world-famous road that runs through town. Thousands of shiny vintage vehicles, nearly 80,000 spectators, stages with live music and scores of commercial vendors catering to classic car dealers, collectors and spectators line the streets of Springfield’s historic centre.

Nestled in the heart of the Midwest, St. Louis blends classic all-American appeal with a modern, cosmopolitan edge – all at an affordable price point. Captivating attractions, world-class sports, surprising histories and a culinary scene that will tantalize your taste buds are just the beginning of what you’ll discover in this friendly Missouri city.

Perhaps St. Louis’ most recognizable landmark, the awe-inspiring Gateway Arch commemorates the city’s role in the westward expansion of the USA. Soar to new heights – 192 meters, to be exact – aboard an enclosed tram to the top, where you’ll take in breath-taking panoramic views of the city and the Mississippi River below. Take time to wander the museum at the base of the Arch to learn more about the area’s history then explore the beautifully landscaped park grounds. Nearby, the National Blues Museum is the only attraction of its kind dedicated to preserving the rich history and global influence of blues music through immersive multimedia installations. Get to know this iconic U.S.-born musical style in four distinct exhibit halls, each archiving captivating artifacts and electrifying live performances from blues history.

If you’re looking to embark on a classic U.S. adventure along historic Route 66, St. Louis makes an excellent entry point for a journey down the legendary highway. Take a scenic stroll across the Old Chain of Rocks Bridge to see where Route 66 once crossed the mighty Mississippi River. Make a stop at the National Museum of Transportation to get a glimpse of the old-timey cars that travelled the Mother Road in its heyday.

Sports fans will also find plenty to cheer about on a trip to St. Louis. “America’s pastime” is centre stage at Busch Stadium, the home field for the beloved St. Louis Cardinals Major League Baseball team. After the game, make your way to Ballpark Village, a vibrant entertainment complex just across the street from the stadium, to enjoy shopping, dining and a deep dive into baseball history at the Cardinals Hall of Fame. Baseball isn’t the end of the story when it comes to St. Louis’ sports scene. The St. Louis CITY Soccer Club and St. Louis Blues Hockey Team both enjoy fervent support from their dedicated fan bases.

Springfield is a town of many legacies and reputations, from its prominent role in Route 66 history to its nickname "the City of the Ozarks." These stories are celebrated all across the city, at annual festivities and year-round attractions alike. Find intriguing road trip stops, a diverse culinary scene and unique shopping, all in an atmosphere that radiates classic Americana heritage. In Springfield, you can enjoy out-of-the-ordinary experiences while still feeling right at home.

Springfield is recognized as the official Birthplace of Route 66. The historic “Mother Road” linking Chicago, Illinois, and Los Angeles, California, got its name during a meeting of highway officials there in 1926. History buffs will want to cruise along local portions of the famous highway to see colourful murals and neon signs that bring the Mother Road to life. Dive deeper into the road’s history by checking out exhibits at the History Museum on the Square and classic cars at the Route 66 Car Museum. Venture just outside town to explore Gary’s Gay Parita, a charmingly restored 1900s gas station in nearby Ash Grove. Visit during August to celebrate the iconic highway with live music, car shows and a parade at the annual Birthplace of Route 66 Festival.

Much of Springfield’s charm lies in its duality: It’s just as easy to enjoy cultural pursuits in a bustling downtown as it is to get outside and experience nature. Kayak or paddleboard on peaceful waterways, bike scenic trails and soak in the splendor of Missouri's Ozark Mountains. The natural jewel of the area is Fantastic Caverns, the only cave system in North America large enough to accommodate a Jeep-drawn tram tour.

Back in town, Springfield’s arts scene is full of character. Catch a live performance at the historic Landers and Gillioz Theatres, then hit the streets of downtown to admire public art along Sculpture Walk Springfield. When hunger strikes, treat yourself to the city’s unique flavours. Dig into a plate of famed Springfield-style cashew chicken or try local favourites like Cafe Cusco or Black Sheep Burgers.

Tulsa, the second-largest city in Oklahoma, is both cosmopolitan and all-American in its appeal. It’s a place of contrasts along the Arkansas River, where Art Deco architecture sits alongside steel skyscrapers, and rural Route 66 Americana meets state-of-the-art entertainment. Tulsa is a city of many cultures, where diverse influences converge to shape a distinct identity. Plan a visit to explore how Tulsa is preserving its history and innovating for the future.

Take an old-fashioned cruise along Tulsa’s 45 kilometers of Route 66, where you can still spot landmarks from the Mother Road’s heyday. Soak in the nostalgic vibes as you admire over 250 neon signs around town, many of which have been lighting up Tulsa’s streets since the early- to mid- 1900s. Head to Tulsa Expo Square to snap a photo with the impressive Golden Driller, a 23-meter-tall statue erected in 1966 as a tribute to Tulsa’s oil workers. The Driller is far from the only larger-than-life sculpture you can find along Route 66. During the Mother Road’s heyday, many businesses installed attention-grabbing “muffler men” – large, whimsical fiberglass statues – to advertise to drivers traveling the route. While only a few originals have survived, many Tulsa businesses sport recreations of the classic figures. Some popular homages to the muffler men of old include Buck and Stella Atom, the cowboy and cowgirl pair who welcomes visitors to iconic souvenir stop Buck Atom’s Cosmic Curios on 66, and Meadow Gold Mack, a lumberjack who stands watch over the local vendor stands at Meadow Gold Mack’s Route 66 Outpost. Find even more Oklahoma Route 66 must-sees just outside town – the Blue Whale of Catoosa is about a 20-minute drive east, and the Tee-Pee Drive-In movie theatre is west in Sapulpa.

Tulsa is home to a growing number of unique main streets and destination districts. The Historic Greenwood District is known as “Black Wall Street” for its legacy as one of the USA’s most prosperous Black communities. Despite the violence of the 1921 Tulsa Race Massacre, this district continues to flourish as a hub for Black business, culture and history. Don’t miss the award-winning Greenwood Rising Black Wall Street History Centre, a state-of-the-art facility that brings the story of Greenwood to life through immersive exhibits. Nearby, the diverse Kendall Whittier Neighbourhood's offerings range from the Circle Cinema – the city’s oldest-standing independent movie theatre – to local art galleries, breweries and authentic Mexican restaurants.

Downtown Tulsa is a walkable hot spot for shopping, dining and entertainment, including the Tulsa Arts District which features the city’s largest selection of music venues and art galleries. Enjoy art crawls and free entertainment in the community park Guthrie Green and see live music at historic venues like Cain’s Ballroom. Nearby, the famed Blue Dome District offers a vibrant dining and nightlife scene. It’s a great spot for foodies to indulge in James Beard award-winning cuisine, as are the neighbouring shopping and dining districts of Cherry Street and Brookside.

Oklahoma City, known colloquially as OKC, is a bustling metropolis with a pioneer heart. With about 630,000 residents, it’s got all the big-city amenities you’d normally find in a state capital – fine dining, intriguing museums and top-notch performing arts – but you can easily become immersed in the city’s Old West heritage via its many cowboy-themed restaurants, shops and activities, too.

Oklahoma City may be a big Midwestern city, but you’d be forgiven for thinking you were in an Old West cowboy town. For example, at the Stockyards City auction house you can see live cattle auctions, then enjoy a hearty steak dinner at Cattleman's Steakhouse before heading to the Rodeo Opry. Oklahoma City is also known as the "Horse Show Capital of the World," and competitions can be seen at State Fair Park. If you want to dress the part, pick up some western attire at Langston's Western Wear, Joe's Boots or the Outlet Shoppes at Oklahoma City.

One of the most popular – and unusual – museums in Oklahoma City is the Museum of Osteology, which houses over 300 human and animal skeletons. Other unlikely but intriguing museums include the American Pigeon Museum and the Oklahoma State Firefighters Museum. Art buffs love the permanent and rotating exhibits at Oklahoma City Museum of Art and Oklahoma Contemporary Arts Centre. To learn about famous Oklahomans such as singers Reba McEntire and Blake Shelton, head to the Oklahoma Hall of Fame at the Gaylord-Pickens Museum. To delve into OKC’s Western heritage and pioneer roots, spend an afternoon at the American Banjo Museum, the National Cowboy and Western Heritage Museum or the Land Run Monument. And you cannot visit the city without paying your respects at the Oklahoma City National Memorial & Museum, which honours the victims, survivors and rescuers of the 1995 bombing of the Alfred P. Murrah Federal Building, in which 168 people lost their lives.

Pull on your cowboy boots and prepare for excitement in Amarillo, Texas. This eclectic Panhandle city shines with an inviting mix of Old West heritage and artistic energy. Here, you can explore Palo Duro Canyon State Park on horseback or watch cowboys and cowgirls compete at championship rodeos; cruise past vintage storefronts in the Route 66 Historic District or gaze at contemporary works in the Amarillo Museum of Art; walk in the footsteps of a legendary rancher at the Charles Goodnight Historical Centre or purchase Western attire from artisan shops. No matter the purpose or season of your visit, your Wild West adventure awaits in Amarillo.

Amarillo is the largest city on the 286-kilometer section of Route 66 that runs from Oklahoma to New Mexico. Fans of Route 66 can relive the Mother Road’s glory days in the Route 66 Historic District, where art galleries, antique shops and restaurants brighten original buildings with Western flair. The walkable district is a popular place to take photos, shop for souvenirs and learn about must-see spots nearby.

One such Route 66 attraction is the famed Cadillac Ranch. This interactive installation – featuring 10 classic Cadillacs half-buried in the ground – invites you to add your spray-painted mark to the artwork guests have made over the years. A few kilometers away, Bill’s Backyard Classics presents a warehouse full of preserved and restored hotrods, and the free Jack Sisemore RV Museum showcases recreational vehicles from the 1930s through the '70s. It’s all in a day’s drive from Downtown Amarillo.

As soon as you set foot in Santa Fe, you will realize it is unlike anywhere else. With its rich history and heritage that includes Native American, Spanish, Mexican, cowboy, artistic and modern U.S. cultures, Santa Fe is among the nation’s most unique cities. You’ll discover that it definitely is one of the most interesting, and was named by Conde Nast Traveller magazine as a "Best Small City."

Centrally located in the Rocky Mountains of northern New Mexico, Santa Fe has attracted artists, hikers, seekers, skiers and writers to its temperate climates and abundant scenery.

Founded in the early 1600s, Santa Fe is one of the oldest cities in the USA, as well as the oldest and highest-elevation state capital (2,200 meters above sea level). New Mexico’s oldest city retains a sophisticated feel – its Santa Fe style.

In Santa Fe, colourful open-air marketplaces, ancient buildings (the Palace of the Governors, for example, is the nation’s oldest continuously occupied public building), art galleries and museums sit side-by-side with sleek restaurants, exciting nightclubs and modern hotels. The plaza in downtown Santa Fe is filled with modern stores of all kinds situated alongside the Native American art market, which takes place underneath the portal at the Governor’s Palace.

Outside the city, highlights include Bandelier National Monument, which protects more than 13,000 hectares of canyon and mesa with petroglyphs, dwellings and masonry of indigenous cultures dating back more than 11,000 years. Or, travel the High Road to Taos, a 170-kilometer trip through the Sangre de Cristo Mountains dotted with Spanish Colonial and Pueblo Indian villages where you can tour historic buildings and shop for authentic crafts.

Nestled in spectacular red rock beauty and located along historic Route 66, Gallup is a beautiful place that offers enticing outdoor adventures while seamlessly blending awe-inspiring art and rich culture deeply rooted in Native American tradition and its People.

The Gallup area thrived as a crossroads of Native American trade long before the City itself came along. Known as Na'Nizhoozhi, or "The Bridge" among the Navajo/Dine' people, Gallup's history began well before the city was founded in 1881 as a headquarters for the southern transcontinental rail route, and continued to grow to the unique destination it is today.

Gallup is the epicenter of Native American Art: over 70% of the authentic Native American Art in the world comes from the Gallup region produced by over five tribes in the region. This fantastic art is encouraged and celebrated through the Gallup Inter-tribal Indian Ceremonial, the Gallup Native Arts Market, and the Second Street Arts Festival. Gallup boasts over 30 miles of hiking and biking trails all just minutes from the downtown area, and even more renowned trails as you venture deeper into the region. The Gallup region is also home to some incredibly unique fusion cuisine- a marriage between New Mexican chile based dishes, Mexican recipes, and Native American style foods from the tribes surrounding the city. 

Gallup Antelope DancersImmerse yourself in Native American Culture with the Nightly Indian Dances (from Memorial Day through Labour Day) for free in the heart of downtown Gallup, or in August at the annual Gallup Inter-Tribal Indian Ceremonial or the Gallup Native Arts Market. You’ll be on the edge of your seat watching real cowboys take on the roughest bulls at the Wild Thing Championship Bull Riding event in July or with the Lions Club Rodeo in June of every year. Feel the heat of hot air balloons, hot cars, and hot Harleys with our Route 66 Freedom Ride, Flight, and Cruise event on the last weekend of July. Reach incredible heights with the best photography in the region by flying over or climbing the red rocks at the Red Rock Balloon Rally the first weekend of December.

Travellers have made memories in Winslow for the past century, first as a stop along the Santa Fe Railroad then as overnight rests on Route 66 road trips. Interstate 40 now routes traffic around Winslow, but savvy road trippers know there are many “fine sites to see” just a mile south in the historic downtown district. Old brick buildings that date back to the railroad era line the main drag, where a flatbed Ford permanently parked on the corner immortalizes the town’s identity.

Iconic selfies await in Winslow. The 9/11 Memorial Park near the east entrance to town is a great place to pull over and get a shot of the Route 66 sign that welcomes visitors. At 2nd Street and Kinsley Avenue in the historic district, Standin’ on the Corner Park pays tribute the Eagles tune that put Winslow’s stretch of Route 66 in the history books. Snap a shot with the Jackson Brown statue (he wrote “Take it Easy” with the Eagles’ Glenn Frey). Check out the visitor centre located in a former Hubbell Trading Post before strolling blocks lined with gift shops, restaurants and watering holes along historic Route 66.

Winslow’s center-piece is undoubtedly La Posada Hotel, built in 1929. It is considered the last great Fred Harvey hotel built by the Santa Fe Railroad and the Southwestern masterpiece of architect Mary Jane Colter. Visitors can walk through lush courtyards and a fascinating labyrinth of interior corridors and staircases that reach gathering rooms and private nooks, all decorated with period furnishings and artifacts. Visitors come from around the region to dine at the Turquoise Room and shop at the on-site trading post. The original train depot on-site now houses the extraordinary Affeldt Mion Museum, which honours the good citizens who preserved La Posada to its original elegance and ultimately kept Winslow on the map.

Winslow’s location on the southern fringe of the Navajo and Hopi communities makes it a great launching point to explore tribal lands. At Homolovi State Park, visitors can walk to archeological sites attributed to Hopi ancestors. Head deeper into Navajo Nation to tour ancestral pueblos and explore astonishing landscapes. In town, Old Trails Museum specializes in Navajo and Hopi art and chronicles the impact of the Santa Fe Railroad and Route 66 on the colourful character of Winslow. Back at the Affeldt Mion Museum, see the largest hand-spun Navajo rug known to exist.

Nestled in Arizona's rugged and remote wilderness, this tiny town's rich Wild West history comes to life with staged shootouts, wooden sidewalks and a bounty of burros that roam freely. At first glance, the wild burros of Oatman seem to steal the show but dig a bit deeper and you'll discover the town's raucous mining history and a vibrant main street that plays host to various events throughout the year.

Running right through the middle of Oatman is a stretch of the historic Route 66, the famous road that was the main highway route across the United States from the 1920s through the 1950s. Be sure to explore the road in the afternoon, as the Oatman Ghost Rider Gunfighters put on two free shows daily. The friendly performers ask the crowd to gather around in the street while they act out a heist, complete with loud gunshot blanks. And don't forget to pick up a souvenir or two—from biker gear and mining memorabilia to donkey puppets and Southwestern art, you can find it all in the shops that line the town’s main drag.

Oatman is best known for its beloved burros—small donkeys descended from miners' beasts of burden. The town is home to more burros than people, and it's not unusual to see dozens of donkeys in Oatman wandering the main drag, sticking their heads through the rails along the wood-plank sidewalks, nudging people for treats and otherwise delighting visitors. The burro has become such an integral part of Oatman's identity that the town now plays host to an annual Burro Biscuit Toss, where residents and visitors alike compete to see who can throw a dried-out, gold-painted burro dropping the farthest.

History buffs can learn all about Oatman's mining boom days at the Oatman Hotel (formerly the Durlin). The historic hotel today houses a bar and restaurant on the ground level and a museum on the second floor—including the Clark Gable/Carole Lombard honeymoon suite. Patrons have placed one-dollar bills on the saloon's walls and ceiling for decades, a tradition that continues today.

The traditional and most recognized end of Historic Route 66 is the Santa Monica Pier in Santa Monica, California, though the official, original route ended at 7th and Broadway in downtown Los Angeles. The iconic "End of the Trail" sign, a popular photo spot, is located on the pier.  

One of the world's most diverse cities, Los Angeles is home to countless global cultures and distinctive neighborhoods, each offering something exciting. The city has so much going on that you'll want to give yourself plenty of time to explore. If you're after glamour, bustle and excitement, Los Angeles is the place for you.

Start with the storied attractions of Hollywood, such as the Walk of Fame, TCL Chinese Theatre and the Dolby Theatre, before strolling the section of Sunset Boulevard known as The Strip with its vibrant billboards, restaurants and famous nightclubs.

Music lovers will feel right at home in Downtown's L.A. LIVE complex, home to the GRAMMY Museum, which features exhibits and memorabilia tracing the history of popular music. Keep the vibes going at Crypto.com Arena, which hosts high-octane concerts. It's also where you'll go to watch professional sports teams like the National Basketball Association's Lakers, the Women's National Basketball Association's Sparks, and the National Hockey League's Kings.

Families won’t want to miss Universal Studios Hollywood for theme-park thrills, movie attractions such as The Wizarding World of Harry Potter™ and Jurassic World, mind-blowing Super Nintendo World™ and the famed Studio Tour.

Start with the storied attractions of Hollywood, such as the Walk of Fame, TCL Chinese Theatre and the Dolby Theatre, before strolling the section of Sunset Boulevard known as The Strip with its vibrant billboards, restaurants and famous nightclubs.

Everyone in Los Angeles has a favourite beach, and each beach has its own vibe, from the famed Malibu to lively Manhattan Beach, Hermosa Beach and Redondo Beach.

Santa Monica’s 5.6-kilometer stretch of sand is marked by the world-famous pier. The pier – with its amusement park, arcade and aquarium – is a short walk from Santa Monica’s Third Street Promenade, an outdoor mall offering shopping in a festive environment.

Neighbouring Venice Beach is equally enchanting, but at the same time, a world apart. The beach is spacious and the bustling Boardwalk boasts an eclectic mix of locals, Muscle Beach, a skate park and famous outdoor basketball courts.

Beverly Hills and Rodeo Drive - Synonymous with high-fashion shopping and high-end dining, Beverly Hills is an ideal locale for window-shopping single-name stores, such as Chanel, Dior, Gucci, Lanvin, Tiffany’s and Valentino.

This is also a place to people-watch: Sip a latte outside one of the cafes on the palm tree-lined sidewalks and watch the luxury cars roll by, or see if you can spot one of the many celebrity residents disguised as everyday people.

Cultural Institutions - Another fantastic place to see stars – and panoramic views of the city – is the Griffith Observatory atop a hill in Griffith Park northwest of Downtown. 

Exposition park is home to several world-class museums. Check out the California African American Museum, California Science Center, Natural History Museum and the upcoming Lucas Museum of Narrative Art. Do some more museum hopping in Mid-City's Museum Row. Visit the Academy Museum of Motion Pictures, which houses more than 13 million cinematic objects; the Los Angeles County Museum of Art, home to more than 120,000 works representing ancient and modern culture; the Craft Contemporary, with its unique exhibits of handmade art; the Page Museum, home to the La Brea Tar Pits, and the Petersen Automotive Museum, a can't-miss for car enthusiasts. 

On the Westside, there's the Getty Center with its soaring architecture and cosy museum rooms full of sought-after permanent and traveling art exhibits. Stop by the Skirball Cultural Center, one of the world's most dynamic Jewish cultural institutions; and the Hammer Museum, renowned as a showcase for emerging artists.